Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
Wailea vacation rentals combine the comfort of home with the indulgence of resort amenities. Whether you prefer a villa with sunset views, a quiet garden retreat, or a beachside condo steps from the surf, Wailea's neighborhoods cater to every kind of traveler.
Top Wailea Vacation Rental Communities
Oceanfront and Beach Access Villas
- Wailea Beach Villas – oceanfront penthouses and beachfront villas
- Polo Beach Club – beachfront condos with panoramic views
- Wailea Point Village – gated luxury with prime oceanfront location
- Mana Kai Maui – beachfront condos on Keawakapu Beach
- Wailea Elua Village – beachfront property with pavilion and pools
Resort-Style Villas & Upscale Condos
- Ho'olei at Grand Wailea – spacious 3-bedroom villas with cascading pool
- Wailea Ekahi Village – low-rise condos with ocean views and tropical gardens
- Wailea Ekolu Village – hillside condos near golf and beaches
- Wailea Grand Champions Villas – golf course condos with pools
- The Palms at Wailea – Mediterranean-style condos with large lanais
Why Stay in Wailea?
- Access to Wailea Beach, Polo Beach, and Keawakapu Beach
- Home to Wailea Golf Club and scenic coastal trails
- Upscale dining and retail at The Shops at Wailea
- Quiet, landscaped communities perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
Wailea Beach Villas PH403 - 3 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 403 offers a luxurious escape with stunning ocean views and ample space for the whole family. Spanning 2,000 square feet, this penthouse features three bedrooms and three full bathrooms, making it an ideal holiday retreat. Guests can enjoy...
Chic Coastal Living in the Heart of Wailea
This is a NEW listing and it's gorgeous! We are confident you will have a great experience. Welcome to Palms at Wailea 2206 | Your Perfect Hawaiian EscapeStep inside and be instantly captivated by breathtaking views that draw you out to the spacious private lanai....
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802n
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated second-floor, 1-bedroom, 2-bathroom oceanfront condo located in one of Wailea’s most desirable beachfront...
Wailea Ekahi Village 52D - 1 Bedroom Garden View Condo
Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...
Wailea Elua Village 706 - 2 Bedroom Ocean View Condo
Welcome to your dream vacation retreat in Wailea! As you step inside the newly renovated Wailea Elua 706, you\'ll immediately be captivated by the spacious and thoughtfully designed interior. The open concept living area is flooded with natural light, creating a warm...
Wailea Beach Villas PH404 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho\'olawe and...
Wailea Ekahi Village 54B - 1 Bedroom Garden View Condo
Wailea Ekahi 54B is a luxurious one-bedroom two-bathroom vacation rental offering an exceptional blend of comfort and elegance, set within the stunning Wailea Ekahi Village. This inviting ground floor condo boasts a prime location with direct access to lush, tropical...
Wailea Elua Village 707 - 2 Bedroom Ocean View Condo
Ideally situated in a quiet corner along the northern edge of the resort, Wailea Elua Village 707 is just a short stroll to the beachfront pavilion with swimming pool. This vacation rental in the heart of Wailea offers guests a comfortable and upgraded home which...
Wailea Ekahi Village 6F - 1 Bedroom Garden View Condo
Wailea Ekahi Village 6F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo located within the resort community of the Wailea Ekahi Village, a low-density collection of condo clusters set across 34 acres of beautifully...
Wailea Ekolu Village 1203 - 1 Bedroom Ocean View Condo
Wailea Ekolu Village condo #1203 is an exquisite one-bedroom, two-bathroom ocean view retreat designed for discerning travelers seeking the best of Wailea. This sanctuary offers a seamless indoor-outdoor living experience, allowing guests to enjoy breathtaking panoramic...
Wailea Beach Villas PH508 - 3 Bedroom Ocean View Penthouse
Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique layout—perched at the top of the Wailea Beach Villas with sweeping ocean views, soaring ceilings, and a spacious design...
Wailea Ekolu 1608 | 1 Bedroom | Prime Wailea Location with Golf Course Views
Experience the beauty and convenience of Wailea from this tastefully appointed 1-bedroom, 2-bath condo at Wailea Ekolu 1608. Perfectly situated along the fairway of Wailea’s prestigious Blue Golf Course, this ground-level home offers comfort, privacy, and stunning...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Wailea Grand Champions 102 - 2 Bedroom Golf Course View Condo
Welcome to Wailea Grand Champions 102, a luxurious 2-bedroom, 2-bathroom residence nestled between the fairways of one of Maui\'s most popular championship golf courses. This spacious second-floor unit, spanning over 1,400 square feet, offers a perfect blend of privacy...
Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium #2503
Yes, you can enjoy a holiday and vacation stay at Wailea Point, the iconic red roofs on Maui's wonderful southern shore; and at a rate lower than a suite at the Wailea hotels. 2503 just may be the 'best location in the whole property'; with an expansive outdoor lanai...
Wailea Grand Champions 140 - 2 Bedroom Garden View Condo
Wailea Grand Champions 140 is a remarkable vacation rental nestled in the upscale Wailea community of Maui. This charming property combines elegance with comfort, offering a luxurious retreat that is perfect for both relaxation and adventure. Upon entering Wailea Grand...